I think trading for Middleton is more realistic, but still very pricy...
Middleton can't be traded until Jan 14th, but he's be a fantastic fit here. He's a great shooter and a solid defender. He's sort of blowing up right now, though (back to back 33+ point games). His usage was really low early in the season and I think the Bucks are coming to the realization that he's maybe their only capable shooter. Over his past 11 games he's averaged 21 points, 4.9 assists, 3.6 rebounds and 1.3 steals.
Last 5 he's averaged 25 points, 5 assists, 3.8 rebounds with 59%/61%/89% shooting (averaging 3.4 threes per night)... I mean... he can't sustain that, obviously. Those shooting percentages are ridiculous. But he shot 47%/41%/86% last year and this year he's shooting 43%/46%/89% (he had a slow start).
Middleton's play is partially why I think Jabari could actually maybe be moved. You'd have to overpay to get Jabari, but right now Jabari is barely being used. He's mostly getting dunks on the cuts to the rim. They aren't running anything through him really. This is a guy who has a future as a really dynamic offensive weapon (similar to Melo), and he's basically a nonfactor in their system right now.
Maybe MIddleton would be traded instead, but they'd be desperate for some shooting. There's really nobody on that team capable of hitting threes other than him. That said, he's one of those guys who was possibly available in free agency this Summer, but the Bucks kept him (hence why he can't be traded until Jan 14th)... but with those guys you always have to question whether they were retained simply because they didn't want to let an asset leave for nothing... or if they actually intended to keep them long-term. If they are committed to Jabari, they could maybe move MIddleton (15 mil per year). But I still think Jabari and Giannis is going to be an awkward fit long-term. I've semi wondered for the past couple years if there's a Philly/Bucks trade sitting there. Philly has centers. Bucks have small forwards. I wonder if they could make something happen that is mutually beneficial. Yeah the Bucks have Monroe, but I always thought Monroe was more of a PF.